Structure elucidation of 11-amino-8-hydroxypentacyclo[5.4.0.02, 6.03, 10.05, 9]undecane-8,11-lactam through selective acetylation and complete 1H and 13C NMR spectral assignment of the mono-, di- and triacetates
✍ Scribed by F. J. C. Martins; A. M. Viljoen; H. G. Kruger; P. L. Wessels
- Publisher
- John Wiley and Sons
- Year
- 2004
- Tongue
- English
- Weight
- 127 KB
- Volume
- 42
- Category
- Article
- ISSN
- 0749-1581
- DOI
- 10.1002/mrc.1355
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✦ Synopsis
Abstract
NMR techniques cannot unambiguously distinguish between 11‐amino‐8‐hydroxypentacyclo[5.4.0.0^2, 6^.0^3, 10^.0^5, 9^]undecane‐8,11‐lactam and 8‐amino‐11‐hydroxypentacyclo[5.4.0.0^2, 6^.0^3, 10^.0^5, 9^]undecane‐8,11‐lactam, both of which are possible products during the reaction of pentacyclo[5.4.0.0^2, 6^.0^3, 10^.0^5, 9^]undecane‐8,11‐dione with Strecker reagents. Treatment of 11‐amino‐8‐hydroxy‐pentacyclo[5.4.0.0^2, 6^.0^3, 10^.0^5, 9^]undecane‐8,11‐lactam with acetic anhydride at room temperature produced a monoacetate. With acetic anhydride containing sodium acetate, a triacetate was obtained at reflux temperature. Treatment with acetyl chloride and N,N‐dimethylaniline produced a diacetate. High‐field ^1^H and ^13^C NMR techniques were used in the structure elucidation and assignment of the different NMR resonances of these three acetylated compounds. Copyright © 2004 John Wiley & Sons, Ltd.